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GB1511559A - Anthracycline glycosides - Google Patents

Anthracycline glycosides

Info

Publication number
GB1511559A
GB1511559A GB39471/75A GB3947175A GB1511559A GB 1511559 A GB1511559 A GB 1511559A GB 39471/75 A GB39471/75 A GB 39471/75A GB 3947175 A GB3947175 A GB 3947175A GB 1511559 A GB1511559 A GB 1511559A
Authority
GB
United Kingdom
Prior art keywords
resulting
derivative
tetradeoxy
trifluoroacetamido
threo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB39471/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Italia SRL
Original Assignee
Farmaceutici Italia SpA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA
Priority to GB39471/75A priority Critical patent/GB1511559A/en
Priority to US05/722,689 priority patent/US4067969A/en
Priority to NLAANVRAGE7610139,A priority patent/NL174015C/en
Priority to AU18025/76A priority patent/AU504480B2/en
Priority to DK426076A priority patent/DK146626C/en
Priority to CA261,920A priority patent/CA1060002A/en
Priority to DE2642837A priority patent/DE2642837C3/en
Priority to FR7628582A priority patent/FR2325659A1/en
Priority to SE7610564A priority patent/SE429655B/en
Priority to AT707276A priority patent/AT347582B/en
Priority to BE170901A priority patent/BE846548A/en
Priority to CH1215876A priority patent/CH606082A5/xx
Priority to SU762403408A priority patent/SU670226A3/en
Priority to ZA765736A priority patent/ZA765736B/en
Priority to JP51115356A priority patent/JPS5242869A/en
Priority to SU772523451A priority patent/SU730310A3/en
Priority to AT68278A priority patent/AT348128B/en
Publication of GB1511559A publication Critical patent/GB1511559A/en
Priority to SE8001616A priority patent/SE435514B/en
Priority to HK11/82A priority patent/HK1182A/en
Priority to DK548982A priority patent/DK147260C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)

Abstract

1511559 Daunomycin and adriamycin derivatives SOC FARMACEUTICI ITALIA SpA 21 Sept 1976 [26 Sept 1975] 39471/75 Heading C2C Novel 4<SP>1</SP>-deoxy-daunomycins of the general formula wherein R 1 =R 3 =H and R 2 is H, methyl, methoxy, Cl or Br; R 1 = R 2 = H and R 3 is C 1-4 alkoxy; or R 2 =H and R 1 and R 3 are methyl, methoxy, Cl or Br, are prepared by condensing an aglycone of the general formula with 2,3,4,6 - tetradeoxy - 3 - trifluoroacetamido - L - threo - hexopyranosyl chloride, followed by removal of the protecting group. They may be brominated and the resulting 14 - bromo derivative hydrolysed to give the corresponding novel adriamy cin derivative. 2,3,4,6 - Tetradeoxy - 3 - trifluoroacetamido - L- threo-hexopyranosyl chloride is prepared by reacting methyl N - trifluoroacetyl - daunosaminide with methanesulphonyl chloride, treating the resulting 4-O-mesyl derivative with sodium iodide, hydrogenating catalytically the resulting 4 - desoxy - 4 - iodo derivative, hydrolysing the resulting 4-desoxy derivative with an acid, treating the resulting 2,3,4,6-tetradeoxy-3- trifluoroacetamido - L - threo - hexopyranose with p-nitrobenzoyl chloride and reacting the resulting 1-p-nitrobenzoate with HCl.
GB39471/75A 1975-09-26 1975-09-26 Anthracycline glycosides Expired GB1511559A (en)

Priority Applications (20)

Application Number Priority Date Filing Date Title
GB39471/75A GB1511559A (en) 1975-09-26 1975-09-26 Anthracycline glycosides
US05/722,689 US4067969A (en) 1975-09-26 1976-09-13 Anthracycline glycosides, their preparation and use
NLAANVRAGE7610139,A NL174015C (en) 1975-09-26 1976-09-13 METHOD FOR PREPARING A TUMOR AND LEUKEMIA-DRUGING MEDICINAL PRODUCT BASED ON A DAUNORUBICIN DERIVATIVE AND ACTIVE COMPOUNDS SUITABLE THEREFOR.
AU18025/76A AU504480B2 (en) 1975-09-26 1976-09-22 Anthracycline glycosides
DK426076A DK146626C (en) 1975-09-26 1976-09-22 ANALOGY PROCEDURE FOR THE PREPARATION OF 4'-DEOXYDA UNOMYCINE
AT707276A AT347582B (en) 1975-09-26 1976-09-23 METHOD FOR PRODUCING THE NEW 4'-DEOXYDAUNOMYCIN
DE2642837A DE2642837C3 (en) 1975-09-26 1976-09-23 Anthracycline glycosides and processes for their preparation
FR7628582A FR2325659A1 (en) 1975-09-26 1976-09-23 NEW ANTITUMOR GLYCOSIDES OF THE ANTHRACYCLINE SERIES AND PROCESS FOR THEIR PREPARATION
SE7610564A SE429655B (en) 1975-09-26 1976-09-23 PROCEDURE FOR PREPARING 4'-DEOXIDAUROMYCINE HYDROCHLORIDE
CA261,920A CA1060002A (en) 1975-09-26 1976-09-23 Process for preparing anthracycline glycosides
JP51115356A JPS5242869A (en) 1975-09-26 1976-09-24 Glycoside compound and preparation thereof
CH1215876A CH606082A5 (en) 1975-09-26 1976-09-24
SU762403408A SU670226A3 (en) 1975-09-26 1976-09-24 Method of producing 4-desoxy daunomycin hydrochloride
ZA765736A ZA765736B (en) 1975-09-26 1976-09-24 Anthracycline glycosides
BE170901A BE846548A (en) 1975-09-26 1976-09-24 NEW ANTITUMOR GLYCOSIDES OF THE ANTHRACYCLINE SERIES AND PROCESS FOR THEIR PREPARATION
SU772523451A SU730310A3 (en) 1975-09-26 1977-09-22 Method of preparing 4'-deoxyadriamycin-hydrochloride
AT68278A AT348128B (en) 1975-09-26 1978-02-01 METHOD OF PREPARING THE NEW 4'-DEOXYADRIAMYCINE
SE8001616A SE435514B (en) 1975-09-26 1980-02-29 PROCEDURE FOR PREPARING 4'-DEOXIADRIAMYCINE HYDROCHLORIDE
HK11/82A HK1182A (en) 1975-09-26 1982-01-14 Anthracycline glycosides
DK548982A DK147260C (en) 1975-09-26 1982-12-10 ANALOGY PROCEDURE FOR PREPARING 4'-DEOXYADRIAMYCINE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB39471/75A GB1511559A (en) 1975-09-26 1975-09-26 Anthracycline glycosides

Publications (1)

Publication Number Publication Date
GB1511559A true GB1511559A (en) 1978-05-24

Family

ID=10409731

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39471/75A Expired GB1511559A (en) 1975-09-26 1975-09-26 Anthracycline glycosides

Country Status (16)

Country Link
US (1) US4067969A (en)
JP (1) JPS5242869A (en)
AT (1) AT347582B (en)
AU (1) AU504480B2 (en)
BE (1) BE846548A (en)
CA (1) CA1060002A (en)
CH (1) CH606082A5 (en)
DE (1) DE2642837C3 (en)
DK (1) DK146626C (en)
FR (1) FR2325659A1 (en)
GB (1) GB1511559A (en)
HK (1) HK1182A (en)
NL (1) NL174015C (en)
SE (2) SE429655B (en)
SU (2) SU670226A3 (en)
ZA (1) ZA765736B (en)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1567456A (en) * 1976-11-16 1980-05-14 Farmaceutici Italia Daunomycin derivatives
GB1550879A (en) * 1976-12-22 1979-08-22 Farmaceutici Italia Antitumour glycosides
US4362720A (en) * 1977-04-14 1982-12-07 Chembiomed Ltd. Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
GB1573037A (en) * 1977-05-05 1980-08-13 Farmaceutici Italia Anthracyclines
GB1573036A (en) * 1977-05-05 1980-08-13 Farmaceutici Italia Anthracyclines
US4201773A (en) * 1978-07-26 1980-05-06 The United States Of America As Represented By The Department Of Health, Education And Welfare 7-O-(2,6-Dideoxy-α-L-lyxo-hexopyranosyl)-daunomycinone, desmethoxy daunomycinone, adriamycinone, and carminomycinone
US4259476A (en) * 1979-04-02 1981-03-31 Kende Andrew S Novel heterocyclic anthracycline compounds
DE3060472D1 (en) * 1979-09-01 1982-07-15 Erba Farmitalia Anthracycline glycosides, processes for their preparation and pharmaceutical composition containing them
CA1174669A (en) * 1980-07-18 1984-09-18 Michael J. Broadhurst Anthracycline glycosides
ZA814722B (en) * 1980-07-18 1982-07-28 Hoffmann La Roche Novel anthracycline glycosides
US4345070A (en) * 1980-09-29 1982-08-17 Farmitalia Carlo Erba S.P.A. Process for the preparation of 4'-deoxy-daunorubicin and 4'-deoxy-doxorubicin
DE3172152D1 (en) * 1980-11-01 1985-10-10 Erba Farmitalia Anthracycline glycosides, intermediate compounds, process for preparing both and pharmaceutical compositions
DE3164763D1 (en) * 1980-11-01 1984-08-16 Erba Farmitalia Anthracycline glycosides, process for the preparation thereof, intermediate compounds and their preparation and pharmaceutical compositions
JPS57142981A (en) * 1981-01-21 1982-09-03 Erba Carlo Spa Anthracycline glycoside, manufacture and tumor generation inhibiting drug containing same
DE3200809C2 (en) * 1981-01-21 1986-08-28 Farmitalia Carlo Erba S.p.A., Mailand/Milano 4'-Deoxy-3'-epi-daunorubicin and -doxorubicin, processes for their preparation and pharmaceuticals containing these compounds
US4325947A (en) * 1981-05-12 1982-04-20 Farmitalia Carlo Erba S.P.A. 4-Demethoxy-4'-deoxydoxorubicin
DE3317702A1 (en) * 1982-05-24 1983-11-24 Farmitalia Carlo Erba S.p.A., 20159 Milano ANTHRACYCLINGLYCOSIDES, METHOD FOR THE PRODUCTION THEREOF, AND MEDICINAL PRODUCTS CONTAINING THEM
US4562177A (en) * 1982-08-17 1985-12-31 The Ohio State University Research Foundation 3'-Amino-2' halo-anthracycline antibiotics
US4514561A (en) * 1983-04-15 1985-04-30 Research Corporation Process for preparing α-L N-acetyl daunosaminide
DE3500023A1 (en) * 1985-01-02 1986-07-10 Farmitalia Carlo Erba S.p.A., Mailand/Milano 4'-Deoxyanthracycline esters
GB2169285A (en) * 1985-01-05 1986-07-09 Erba Farmitalia 4'-Deoxydoxorubicin-14-esters
US5124317A (en) * 1985-08-02 1992-06-23 Farmitalia Carlo Erba S.P.A. Injectable ready-to-use solutions containing an antitumor anthracycline glycoside
GB8519452D0 (en) * 1985-08-02 1985-09-11 Erba Farmitalia Injectable solutions
GB8708927D0 (en) * 1987-04-14 1987-05-20 Erba Farmitalia Chiral synthesis of anthracyclines
NZ224252A (en) 1987-04-21 1991-09-25 Erba Carlo Spa An anthracycline glycoside and its preparation
GB2212154B (en) * 1987-11-10 1991-03-27 Erba Carlo Spa New 4-demethoxy anthracycline derivatives
JPH03502327A (en) * 1988-01-19 1991-05-30 ボード・オブ・リージェンツ，ザ・ユニバーシティ・オブ・テキサス・システム Ester form of 3'-diaminodoxorubicin, its liposome composition, and its use
GB8803076D0 (en) * 1988-02-10 1988-03-09 Erba Carlo Spa 3'-deamino-4'-deoxy-4'-amino anthracyclines
WO1990007519A1 (en) * 1988-12-28 1990-07-12 Board Of Regents, The University Of Texas System 3'-deamino analogs of esorubicin and methods for their use
US5948896A (en) * 1997-08-13 1999-09-07 Gem Pharmaceuticals Processes for preparing 13-deoxy anthracycline derivatives
US5942605A (en) * 1998-03-03 1999-08-24 Gem Pharmaceuticals, Inc. 5-imino-13-deoxy anthracycline derivatives, their uses, and processes for preparing them

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3803124A (en) * 1968-04-12 1974-04-09 Farmaceutici It Soc Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives
DE1792346C3 (en) * 1968-08-22 1980-10-23 Rotta Research Laboratorium S.P.A., San Fruttuoso Di Monza, Mailand (Italien) Pharmaceutical preparation for the treatment of degenerative joint diseases
FR2183710A1 (en) * 1972-05-06 1973-12-21 Farmaceutici Italia Daunomycin (hydrochloride) prepn - by reaction of daunomycinone with daunosamines, useful as antitumour agent and anti-leucemic
US4020270A (en) * 1974-05-02 1977-04-26 Societa' Farmaceutici Italia S.P.A. L-lyxohex-1-enopyranose derivative

Also Published As

Publication number Publication date
ATA707276A (en) 1978-05-15
DK426076A (en) 1977-03-27
CH606082A5 (en) 1978-10-13
FR2325659A1 (en) 1977-04-22
AU1802576A (en) 1978-04-06
DK146626B (en) 1983-11-21
US4067969A (en) 1978-01-10
NL174015C (en) 1984-04-16
CA1060002A (en) 1979-08-07
SE429655B (en) 1983-09-19
DE2642837A1 (en) 1977-04-07
DK146626C (en) 1984-04-30
AU504480B2 (en) 1979-10-18
ZA765736B (en) 1977-11-30
SE435514B (en) 1984-10-01
NL174015B (en) 1983-11-16
SE8001616L (en) 1980-02-29
NL7610139A (en) 1977-03-29
HK1182A (en) 1982-01-22
JPS6123189B2 (en) 1986-06-04
FR2325659B1 (en) 1982-08-20
SU670226A3 (en) 1979-06-25
SU730310A3 (en) 1980-04-25
JPS5242869A (en) 1977-04-04
BE846548A (en) 1977-03-24
AT347582B (en) 1979-01-10
DE2642837B2 (en) 1982-01-07
DE2642837C3 (en) 1982-08-12
SE7610564L (en) 1977-03-27

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PE20 Patent expired after termination of 20 years

Effective date: 19960920